Reaktion #6586

Reaktionsgleichung

N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide

lithium hexamethyldisilazane

phenylacetylene

→

title compound

Ausbeute 34.9%

1-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-one

Ausbeute 34.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePartition between ethyl ether and saturated aqueous sodium chloride
2. 2
   Sonstigeseparate the organic phase
3. 3
   Trocknendry (MgSO4)
4. 4
   FiltrationFilter
5. 5
   Sonstigeevaporate the solvent in vacuo
6. 6
   workup.ADDITIONPour onto silica gel
7. 7
   Waschenelute with 20% ethyl acetate/hexane
8. 8
   Sonstigeto yield a crude solid
9. 9
   SonstigeRecrystallize (hexane/ethyl acetate)

Vorschrift

Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) and tetrahydrofuran (10 mL) under an argon atmosphere and cool to 0° C. Add phenylacetylene (0.33 mL, 3 mmol) and stir at 0° C. for 30 minutes. Add N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide (0.76 g, 3 mmol), remove the cooling bath and stir at room temperature for 1 hour. Partition between ethyl ether and saturated aqueous sodium chloride, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo. Pour onto silica gel and elute with 20% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane/ethyl acetate) to yield 0.31 g of the title compound; mp 94°-96° C.

Quelle